You would think I could find the simple answer to this on Apple.com or via Google, but I am not sure how to deal with this. (I have all my own stuff all as MP3s so I don't have this problem when I ...
Try removing all external devices except your iPod and syncing again. You can also reset your iPod (by pressing the menu button and the center button until the screen goes black and the Apple logo ...
Several users are affected by an issue where iTunes crashes shortly after connecting an iPod. MacFixIt reader Rory Cooney summarizes the problem: "Longtime users of iPods of various pedigree and size, ...